Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Chew Hee Ng' _publ_contact_author_address ; Biosciences and Chemistry Universiti Tunku Abdul Rahman Faculty of Engineering and Science, Kuala Lumpur Wilayah Persekutuan 53300 MALAYSIA ; _publ_contact_author_email NGCH@MAIL.UTAR.EDU.MY _publ_section_title ; Synthesis, characterization, DNA-binding study and anticancer property of ternary metal(II) complexes of EDDA and an intercalating ligand ; loop_ _publ_author_name 'Chew Hee Ng' 'Pauline Balraj' 'Makoto Chikira' 'Hirokazu Hamada' 'Paul Jensen' 'King Chow Kong' ; E.Thirthagiri ; 'Sze Tin Von' data_twh06pj1 _database_code_depnum_ccdc_archive 'CCDC 636037' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (N,N'-ethylenediaminediacetato)(1,10-phenanthroline)copper(II) pentahydrate ; _chemical_name_common ;(N,N'-ethylenediaminediacetato)(1,10- phenanthroline)copper(ii) pentahydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H18 Cu N4 O4, 5(H2 O)' _chemical_formula_sum 'C18 H28 Cu N4 O9' _chemical_formula_weight 507.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1 ' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.897(1) _cell_length_b 11.233(2) _cell_length_c 11.851(2) _cell_angle_alpha 65.609(2) _cell_angle_beta 70.409(2) _cell_angle_gamma 73.771(2) _cell_volume 1115.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7062 _cell_measurement_theta_min 2.2143 _cell_measurement_theta_max 28.2892 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 530 _exptl_absorpt_coefficient_mu 1.036 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.655 _exptl_absorpt_correction_T_max 0.840 _exptl_absorpt_process_details ; Gaussian (Coppens et al., 1965), XPREP (Bruker, 1995) ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker CCD-1000 area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 162 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.07 _diffrn_reflns_number 11229 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.31 _reflns_number_total 5197 _reflns_number_gt 4638 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART Ver. 5.054 (Bruker-AXS, 1998)' _computing_cell_refinement 'SAINT Ver. 6.45 (Bruker-AXS, 2003)' _computing_data_reduction 'SAINT Ver. 6.45' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)' _computing_publication_material 'modiCIFer-12162005 (Guzei, 2005)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+0.2268P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5197 _refine_ls_number_parameters 325 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0313 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0739 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.442298(19) 0.266936(17) 0.302755(17) 0.01775(7) Uani 1 1 d . . . O1 O 0.29509(13) 0.41605(11) 0.15999(11) 0.0264(3) Uani 1 1 d . . . O2 O 0.06778(13) 0.43137(12) 0.15308(11) 0.0279(3) Uani 1 1 d . . . O3 O 0.56711(12) 0.13082(11) 0.45698(10) 0.0208(2) Uani 1 1 d . . . O4 O 0.79796(12) 0.04604(11) 0.46228(11) 0.0248(2) Uani 1 1 d . . . O5 O 0.32812(14) 0.68603(12) 0.06369(11) 0.0296(3) Uani 1 1 d D . . H5A H 0.305(2) 0.6107(12) 0.0985(18) 0.036 Uiso 1 1 d D . . H5B H 0.2636(18) 0.7341(18) 0.0999(19) 0.036 Uiso 1 1 d D . . O6 O 0.03518(14) 0.67271(12) -0.03227(12) 0.0291(3) Uani 1 1 d D . . H6A H 0.010(2) 0.645(2) -0.0750(18) 0.035 Uiso 1 1 d D . . H6B H 0.052(2) 0.6057(14) 0.0297(15) 0.035 Uiso 1 1 d D . . O7 O -0.11787(16) 0.87219(14) 0.05877(14) 0.0392(3) Uani 1 1 d D . . H7A H -0.074(2) 0.8102(17) 0.030(2) 0.047 Uiso 1 1 d D . . H7B H -0.059(2) 0.876(2) 0.093(2) 0.047 Uiso 1 1 d D . . O8 O 0.11657(17) 0.88913(13) 0.14493(13) 0.0390(3) Uani 1 1 d D . . H8A H 0.129(3) 0.9621(14) 0.0853(16) 0.047 Uiso 1 1 d D . . H8B H 0.110(3) 0.900(2) 0.2129(15) 0.047 Uiso 1 1 d D . . O9 O 0.07011(14) 0.92465(13) 0.37145(13) 0.0329(3) Uani 1 1 d D . . H9A H -0.0069(15) 0.9723(19) 0.390(2) 0.039 Uiso 1 1 d D . . H9B H 0.118(2) 0.919(2) 0.4189(18) 0.039 Uiso 1 1 d D . . N1 N 0.52438(14) 0.43189(12) 0.26070(12) 0.0182(3) Uani 1 1 d . . . N2 N 0.29439(14) 0.33429(12) 0.43914(12) 0.0191(3) Uani 1 1 d . . . N3 N 0.32348(14) 0.15034(13) 0.29362(12) 0.0198(3) Uani 1 1 d D . . H3N H 0.3032(19) 0.0814(13) 0.3634(12) 0.024 Uiso 1 1 d D . . N4 N 0.61655(14) 0.17132(12) 0.20569(12) 0.0196(3) Uani 1 1 d D . . H4N H 0.6454(19) 0.2116(17) 0.1237(9) 0.023 Uiso 1 1 d D . . C1 C 0.44310(16) 0.50243(14) 0.33722(14) 0.0178(3) Uani 1 1 d . . . C2 C 0.63711(17) 0.48065(16) 0.16817(15) 0.0234(3) Uani 1 1 d . . . H2 H 0.6925 0.4339 0.1120 0.028 Uiso 1 1 calc R . . C3 C 0.67688(18) 0.59867(17) 0.15073(16) 0.0270(3) Uani 1 1 d . . . H3 H 0.7588 0.6300 0.0845 0.032 Uiso 1 1 calc R . . C4 C 0.59784(19) 0.66819(16) 0.22893(16) 0.0265(3) Uani 1 1 d . . . H4 H 0.6248 0.7477 0.2183 0.032 Uiso 1 1 calc R . . C5 C 0.47514(17) 0.62108(15) 0.32620(15) 0.0216(3) Uani 1 1 d . . . C6 C 0.38552(19) 0.68604(16) 0.41419(17) 0.0272(4) Uani 1 1 d . . . H6 H 0.4068 0.7664 0.4075 0.033 Uiso 1 1 calc R . . C7 C 0.27094(19) 0.63445(16) 0.50669(16) 0.0268(4) Uani 1 1 d . . . H7 H 0.2137 0.6790 0.5644 0.032 Uiso 1 1 calc R . . C8 C 0.23435(17) 0.51425(16) 0.51937(15) 0.0222(3) Uani 1 1 d . . . C9 C 0.11796(18) 0.45463(17) 0.61494(15) 0.0271(4) Uani 1 1 d . . . H9 H 0.0572 0.4948 0.6752 0.033 Uiso 1 1 calc R . . C10 C 0.09343(18) 0.33834(18) 0.62005(16) 0.0287(4) Uani 1 1 d . . . H10 H 0.0153 0.2972 0.6839 0.034 Uiso 1 1 calc R . . C11 C 0.18377(17) 0.28028(16) 0.53089(15) 0.0241(3) Uani 1 1 d . . . H11 H 0.1657 0.1993 0.5358 0.029 Uiso 1 1 calc R . . C12 C 0.32022(16) 0.44909(14) 0.43398(14) 0.0177(3) Uani 1 1 d . . . C13 C 0.18387(18) 0.36893(15) 0.18577(14) 0.0217(3) Uani 1 1 d . . . C14 C 0.18164(18) 0.22243(15) 0.26718(16) 0.0237(3) Uani 1 1 d . . . H14A H 0.1078 0.2149 0.3494 0.028 Uiso 1 1 calc R . . H14B H 0.1523 0.1802 0.2223 0.028 Uiso 1 1 calc R . . C15 C 0.41747(19) 0.09779(16) 0.19206(16) 0.0260(3) Uani 1 1 d . . . H15A H 0.4183 0.1673 0.1066 0.031 Uiso 1 1 calc R . . H15B H 0.3807 0.0219 0.1971 0.031 Uiso 1 1 calc R . . C16 C 0.56851(19) 0.05416(15) 0.21257(16) 0.0251(3) Uani 1 1 d . . . H16A H 0.5680 -0.0167 0.2973 0.030 Uiso 1 1 calc R . . H16B H 0.6355 0.0192 0.1458 0.030 Uiso 1 1 calc R . . C17 C 0.74258(17) 0.13244(16) 0.26021(14) 0.0223(3) Uani 1 1 d . . . H17A H 0.8003 0.2054 0.2188 0.027 Uiso 1 1 calc R . . H17B H 0.8053 0.0537 0.2414 0.027 Uiso 1 1 calc R . . C18 C 0.69717(17) 0.10051(14) 0.40483(14) 0.0193(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02053(10) 0.01558(10) 0.01795(10) -0.00807(7) -0.00276(7) -0.00334(7) O1 0.0332(6) 0.0186(5) 0.0261(6) -0.0019(5) -0.0118(5) -0.0064(5) O2 0.0312(6) 0.0256(6) 0.0280(6) -0.0102(5) -0.0147(5) 0.0039(5) O3 0.0243(6) 0.0206(5) 0.0175(5) -0.0072(4) -0.0045(4) -0.0036(4) O4 0.0263(6) 0.0251(6) 0.0236(6) -0.0068(5) -0.0112(5) -0.0019(5) O5 0.0384(7) 0.0221(6) 0.0234(6) -0.0042(5) -0.0056(5) -0.0061(5) O6 0.0327(7) 0.0241(6) 0.0298(7) -0.0056(5) -0.0089(5) -0.0086(5) O7 0.0466(8) 0.0309(7) 0.0385(8) -0.0133(6) -0.0112(6) -0.0015(6) O8 0.0596(9) 0.0271(7) 0.0299(7) -0.0114(6) -0.0095(7) -0.0064(6) O9 0.0301(7) 0.0382(7) 0.0384(7) -0.0219(6) -0.0140(6) 0.0020(5) N1 0.0198(6) 0.0167(6) 0.0180(6) -0.0064(5) -0.0044(5) -0.0026(5) N2 0.0212(6) 0.0178(6) 0.0175(6) -0.0057(5) -0.0043(5) -0.0034(5) N3 0.0266(7) 0.0156(6) 0.0171(6) -0.0032(5) -0.0081(5) -0.0040(5) N4 0.0259(7) 0.0161(6) 0.0131(6) -0.0040(5) -0.0035(5) -0.0016(5) C1 0.0207(7) 0.0157(7) 0.0178(7) -0.0052(6) -0.0086(6) -0.0005(6) C2 0.0233(8) 0.0228(8) 0.0221(8) -0.0073(6) -0.0030(6) -0.0052(6) C3 0.0261(8) 0.0260(8) 0.0263(8) -0.0040(7) -0.0048(7) -0.0107(7) C4 0.0316(9) 0.0201(8) 0.0304(9) -0.0044(7) -0.0128(7) -0.0091(7) C5 0.0268(8) 0.0174(7) 0.0241(8) -0.0070(6) -0.0128(6) -0.0015(6) C6 0.0380(9) 0.0177(7) 0.0321(9) -0.0119(7) -0.0161(8) 0.0001(7) C7 0.0347(9) 0.0228(8) 0.0273(8) -0.0161(7) -0.0121(7) 0.0055(7) C8 0.0242(8) 0.0234(8) 0.0201(7) -0.0101(6) -0.0098(6) 0.0036(6) C9 0.0271(8) 0.0318(9) 0.0191(8) -0.0122(7) -0.0042(6) 0.0033(7) C10 0.0255(8) 0.0331(9) 0.0201(8) -0.0057(7) -0.0012(6) -0.0048(7) C11 0.0251(8) 0.0236(8) 0.0203(8) -0.0044(6) -0.0041(6) -0.0063(6) C12 0.0197(7) 0.0174(7) 0.0165(7) -0.0060(6) -0.0080(6) 0.0003(6) C13 0.0313(8) 0.0199(7) 0.0153(7) -0.0082(6) -0.0077(6) -0.0013(6) C14 0.0266(8) 0.0207(8) 0.0246(8) -0.0042(6) -0.0111(6) -0.0053(6) C15 0.0383(9) 0.0215(8) 0.0234(8) -0.0112(7) -0.0108(7) -0.0039(7) C16 0.0347(9) 0.0168(7) 0.0238(8) -0.0103(6) -0.0079(7) 0.0013(6) C17 0.0222(8) 0.0210(7) 0.0177(7) -0.0045(6) -0.0037(6) 0.0001(6) C18 0.0273(8) 0.0123(6) 0.0194(7) -0.0042(6) -0.0072(6) -0.0054(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 2.0263(13) . ? Cu1 N2 2.0328(13) . ? Cu1 N1 2.0369(13) . ? Cu1 N3 2.0429(13) . ? Cu1 O3 2.3140(11) . ? Cu1 O1 2.3957(12) . ? O1 C13 1.246(2) . ? O2 C13 1.259(2) . ? O3 C18 1.2450(19) . ? O4 C18 1.2662(19) . ? O5 H5A 0.835(9) . ? O5 H5B 0.836(9) . ? O6 H6A 0.818(9) . ? O6 H6B 0.830(9) . ? O7 H7A 0.843(10) . ? O7 H7B 0.835(10) . ? O8 H8A 0.839(10) . ? O8 H8B 0.844(10) . ? O9 H9A 0.820(9) . ? O9 H9B 0.824(9) . ? N1 C2 1.331(2) . ? N1 C1 1.3584(19) . ? N2 C11 1.333(2) . ? N2 C12 1.3567(19) . ? N3 C14 1.475(2) . ? N3 C15 1.480(2) . ? N3 H3N 0.878(9) . ? N4 C17 1.472(2) . ? N4 C16 1.483(2) . ? N4 H4N 0.868(9) . ? C1 C5 1.400(2) . ? C1 C12 1.434(2) . ? C2 C3 1.402(2) . ? C2 H2 0.9500 . ? C3 C4 1.360(2) . ? C3 H3 0.9500 . ? C4 C5 1.414(2) . ? C4 H4 0.9500 . ? C5 C6 1.433(2) . ? C6 C7 1.354(3) . ? C6 H6 0.9500 . ? C7 C8 1.430(2) . ? C7 H7 0.9500 . ? C8 C12 1.403(2) . ? C8 C9 1.410(2) . ? C9 C10 1.368(3) . ? C9 H9 0.9500 . ? C10 C11 1.397(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C13 C14 1.528(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.507(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.528(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cu1 N2 164.52(5) . . ? N4 Cu1 N1 98.74(5) . . ? N2 Cu1 N1 81.85(5) . . ? N4 Cu1 N3 86.03(5) . . ? N2 Cu1 N3 99.00(5) . . ? N1 Cu1 N3 158.85(5) . . ? N4 Cu1 O3 76.95(5) . . ? N2 Cu1 O3 87.58(5) . . ? N1 Cu1 O3 95.40(4) . . ? N3 Cu1 O3 105.75(5) . . ? N4 Cu1 O1 109.02(5) . . ? N2 Cu1 O1 86.44(5) . . ? N1 Cu1 O1 83.74(5) . . ? N3 Cu1 O1 75.25(5) . . ? O3 Cu1 O1 174.02(4) . . ? C13 O1 Cu1 108.70(10) . . ? C18 O3 Cu1 109.88(9) . . ? H5A O5 H5B 106(2) . . ? H6A O6 H6B 105(2) . . ? H7A O7 H7B 102(2) . . ? H8A O8 H8B 107(2) . . ? H9A O9 H9B 105(2) . . ? C2 N1 C1 118.13(13) . . ? C2 N1 Cu1 129.72(11) . . ? C1 N1 Cu1 112.04(10) . . ? C11 N2 C12 118.27(13) . . ? C11 N2 Cu1 129.56(11) . . ? C12 N2 Cu1 112.14(10) . . ? C14 N3 C15 112.12(12) . . ? C14 N3 Cu1 113.05(9) . . ? C15 N3 Cu1 104.97(10) . . ? C14 N3 H3N 105.1(12) . . ? C15 N3 H3N 106.6(12) . . ? Cu1 N3 H3N 115.0(12) . . ? C17 N4 C16 111.53(12) . . ? C17 N4 Cu1 111.75(9) . . ? C16 N4 Cu1 105.99(10) . . ? C17 N4 H4N 108.0(12) . . ? C16 N4 H4N 102.1(12) . . ? Cu1 N4 H4N 117.1(12) . . ? N1 C1 C5 123.21(14) . . ? N1 C1 C12 116.86(13) . . ? C5 C1 C12 119.92(13) . . ? N1 C2 C3 122.26(15) . . ? N1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? C4 C3 C2 119.84(15) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 119.43(15) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C1 C5 C4 117.09(14) . . ? C1 C5 C6 119.05(15) . . ? C4 C5 C6 123.85(15) . . ? C7 C6 C5 120.92(15) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 121.33(15) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C12 C8 C9 117.29(15) . . ? C12 C8 C7 118.78(15) . . ? C9 C8 C7 123.91(15) . . ? C10 C9 C8 119.36(15) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 119.70(16) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? N2 C11 C10 122.43(15) . . ? N2 C11 H11 118.8 . . ? C10 C11 H11 118.8 . . ? N2 C12 C8 122.94(14) . . ? N2 C12 C1 117.08(13) . . ? C8 C12 C1 119.97(14) . . ? O1 C13 O2 126.25(15) . . ? O1 C13 C14 119.00(14) . . ? O2 C13 C14 114.73(14) . . ? N3 C14 C13 112.98(13) . . ? N3 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 . . ? N3 C14 H14B 109.0 . . ? C13 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? N3 C15 C16 107.48(13) . . ? N3 C15 H15A 110.2 . . ? C16 C15 H15A 110.2 . . ? N3 C15 H15B 110.2 . . ? C16 C15 H15B 110.2 . . ? H15A C15 H15B 108.5 . . ? N4 C16 C15 107.64(12) . . ? N4 C16 H16A 110.2 . . ? C15 C16 H16A 110.2 . . ? N4 C16 H16B 110.2 . . ? C15 C16 H16B 110.2 . . ? H16A C16 H16B 108.5 . . ? N4 C17 C18 112.15(12) . . ? N4 C17 H17A 109.2 . . ? C18 C17 H17A 109.2 . . ? N4 C17 H17B 109.2 . . ? C18 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? O3 C18 O4 125.00(14) . . ? O3 C18 C17 118.87(13) . . ? O4 C18 C17 116.12(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Cu1 O1 C13 106.05(11) . . . . ? N2 Cu1 O1 C13 -74.65(11) . . . . ? N1 Cu1 O1 C13 -156.83(11) . . . . ? N3 Cu1 O1 C13 25.63(10) . . . . ? N4 Cu1 O3 C18 22.56(10) . . . . ? N2 Cu1 O3 C18 -156.77(10) . . . . ? N1 Cu1 O3 C18 -75.19(10) . . . . ? N3 Cu1 O3 C18 104.56(10) . . . . ? N4 Cu1 N1 C2 18.02(14) . . . . ? N2 Cu1 N1 C2 -177.62(14) . . . . ? N3 Cu1 N1 C2 -83.7(2) . . . . ? O3 Cu1 N1 C2 95.61(14) . . . . ? O1 Cu1 N1 C2 -90.33(14) . . . . ? N4 Cu1 N1 C1 -165.84(10) . . . . ? N2 Cu1 N1 C1 -1.48(10) . . . . ? N3 Cu1 N1 C1 92.41(17) . . . . ? O3 Cu1 N1 C1 -88.25(10) . . . . ? O1 Cu1 N1 C1 85.80(10) . . . . ? N4 Cu1 N2 C11 -83.4(2) . . . . ? N1 Cu1 N2 C11 -176.77(14) . . . . ? N3 Cu1 N2 C11 24.60(14) . . . . ? O3 Cu1 N2 C11 -80.97(14) . . . . ? O1 Cu1 N2 C11 99.05(14) . . . . ? N4 Cu1 N2 C12 94.2(2) . . . . ? N1 Cu1 N2 C12 0.89(10) . . . . ? N3 Cu1 N2 C12 -157.74(10) . . . . ? O3 Cu1 N2 C12 96.69(10) . . . . ? O1 Cu1 N2 C12 -83.29(10) . . . . ? N4 Cu1 N3 C14 -139.48(11) . . . . ? N2 Cu1 N3 C14 55.26(11) . . . . ? N1 Cu1 N3 C14 -35.4(2) . . . . ? O3 Cu1 N3 C14 145.28(10) . . . . ? O1 Cu1 N3 C14 -28.61(10) . . . . ? N4 Cu1 N3 C15 -16.97(10) . . . . ? N2 Cu1 N3 C15 177.77(9) . . . . ? N1 Cu1 N3 C15 87.10(17) . . . . ? O3 Cu1 N3 C15 -92.22(10) . . . . ? O1 Cu1 N3 C15 93.89(10) . . . . ? N2 Cu1 N4 C17 -25.7(2) . . . . ? N1 Cu1 N4 C17 65.31(10) . . . . ? N3 Cu1 N4 C17 -135.43(10) . . . . ? O3 Cu1 N4 C17 -28.24(9) . . . . ? O1 Cu1 N4 C17 151.66(9) . . . . ? N2 Cu1 N4 C16 96.0(2) . . . . ? N1 Cu1 N4 C16 -173.00(9) . . . . ? N3 Cu1 N4 C16 -13.74(10) . . . . ? O3 Cu1 N4 C16 93.44(9) . . . . ? O1 Cu1 N4 C16 -86.65(10) . . . . ? C2 N1 C1 C5 -2.3(2) . . . . ? Cu1 N1 C1 C5 -178.90(11) . . . . ? C2 N1 C1 C12 178.47(13) . . . . ? Cu1 N1 C1 C12 1.84(16) . . . . ? C1 N1 C2 C3 2.4(2) . . . . ? Cu1 N1 C2 C3 178.30(12) . . . . ? N1 C2 C3 C4 -0.9(3) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? N1 C1 C5 C4 0.7(2) . . . . ? C12 C1 C5 C4 179.94(13) . . . . ? N1 C1 C5 C6 -177.98(14) . . . . ? C12 C1 C5 C6 1.3(2) . . . . ? C3 C4 C5 C1 0.8(2) . . . . ? C3 C4 C5 C6 179.42(16) . . . . ? C1 C5 C6 C7 -0.2(2) . . . . ? C4 C5 C6 C7 -178.82(15) . . . . ? C5 C6 C7 C8 -0.6(2) . . . . ? C6 C7 C8 C12 0.3(2) . . . . ? C6 C7 C8 C9 178.91(15) . . . . ? C12 C8 C9 C10 -0.3(2) . . . . ? C7 C8 C9 C10 -178.97(15) . . . . ? C8 C9 C10 C11 0.1(2) . . . . ? C12 N2 C11 C10 0.8(2) . . . . ? Cu1 N2 C11 C10 178.32(12) . . . . ? C9 C10 C11 N2 -0.3(3) . . . . ? C11 N2 C12 C8 -1.1(2) . . . . ? Cu1 N2 C12 C8 -179.06(12) . . . . ? C11 N2 C12 C1 177.79(13) . . . . ? Cu1 N2 C12 C1 -0.16(16) . . . . ? C9 C8 C12 N2 0.9(2) . . . . ? C7 C8 C12 N2 179.59(14) . . . . ? C9 C8 C12 C1 -177.97(14) . . . . ? C7 C8 C12 C1 0.7(2) . . . . ? N1 C1 C12 N2 -1.2(2) . . . . ? C5 C1 C12 N2 179.56(13) . . . . ? N1 C1 C12 C8 177.77(13) . . . . ? C5 C1 C12 C8 -1.5(2) . . . . ? Cu1 O1 C13 O2 162.02(13) . . . . ? Cu1 O1 C13 C14 -16.48(16) . . . . ? C15 N3 C14 C13 -87.79(16) . . . . ? Cu1 N3 C14 C13 30.64(16) . . . . ? O1 C13 C14 N3 -6.5(2) . . . . ? O2 C13 C14 N3 174.84(13) . . . . ? C14 N3 C15 C16 167.48(12) . . . . ? Cu1 N3 C15 C16 44.38(14) . . . . ? C17 N4 C16 C15 163.67(13) . . . . ? Cu1 N4 C16 C15 41.84(14) . . . . ? N3 C15 C16 N4 -59.12(16) . . . . ? C16 N4 C17 C18 -86.39(15) . . . . ? Cu1 N4 C17 C18 32.04(15) . . . . ? Cu1 O3 C18 O4 167.65(12) . . . . ? Cu1 O3 C18 C17 -11.18(15) . . . . ? N4 C17 C18 O3 -12.04(19) . . . . ? N4 C17 C18 O4 169.04(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5A O1 0.835(9) 2.019(11) 2.8376(17) 167(2) . O5 H5B O8 0.836(9) 2.065(11) 2.8824(19) 166(2) . O6 H6A O2 0.818(9) 1.923(10) 2.7353(17) 172(2) 2_565 O6 H6B O2 0.830(9) 1.901(11) 2.7105(17) 165(2) . O7 H7A O6 0.843(10) 1.893(10) 2.7355(19) 176(2) . O7 H7B O8 0.835(10) 2.083(11) 2.908(2) 169(2) . O8 H8A O7 0.839(10) 1.944(11) 2.769(2) 168(2) 2_575 O8 H8B O9 0.844(10) 1.905(10) 2.7443(19) 173(2) . O9 H9A O4 0.820(9) 1.932(11) 2.7364(17) 167(2) 1_465 O9 H9B O4 0.824(9) 2.060(11) 2.8631(17) 165(2) 2_666 N3 H3N O4 0.878(9) 2.071(10) 2.9256(18) 164.1(17) 2_656 N4 H4N O5 0.868(9) 1.998(10) 2.8552(18) 169.2(17) 2_665 _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.939 _refine_diff_density_max 0.381 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.059